Glycine → HCID 2060367, compound

HRID 1249297Notes

Reaction equation

HRID 1249297 reaction equation
[NH:1]([C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[C@@H:2]([C:4]([OH:6])=O)[CH3:3].[NH2:17][CH2:18][C:19]([OH:21])=[O:20].[CH2:22](N(CC)CC)C.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>C1COCC1>[NH:1]([C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[C@@H:2]([C:4]([NH:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])=[O:6])[CH3:3]

Participants

7

Reactant 5

HCID 750GlycineHCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 70832N-Cbz-d-alanineHCID 757711-Hydroxybenzotriazole

Product 1

HCID 2060367HCID 2060367, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Z-D-Ala (2.23 g, 10 mmol) and Gly.OMe.HCl (1.26 g, 10 mmol) in THF (50 ml) was chilled to 0° C. and triethylamine (1.01 g, 10 mmol), HOBt (1.35 g, 10 mmol) and DCC (2.06 f, 10 mmol) was added successively at 0° C. with stirring. After stirring for 4 hrs at 0° C., the reaction mixture was stirred at room temperature overnight and the precipitated crystals were filtered and the filtrate was evaporated in vacuo. The residue was extracted with ethyl acetate and the extract was washed with 5% citric acid, 5% NaHCO3 and water successively, and dried over anhyd. Na2SO4. The solvent was removed in vacuo and the resulting solid was recrystallized from ethyl acetate-hexane to give Z-D-Ala-Gly-OMe (26) (2.48 g, 84.4%) as colorless needles, mp 96°-97° C.; [α]D22 23.3° (c=1.0, MeOH): NMR (CDCl3)δ:1.39 (3H, d, J=8 Hz, CH3), 3.76 (3H, s CH3O), 4.03 (2H, d, J=6 Hz, CH2NH), 4.15-4.50 (1H, m, --CH--NH), 5.15, (2H, s, CH2O), 5.58 (1H, d, J=7 Hz, NH), 6.70-6.95 (1H, br, NH), 7.42 (5H, s, Ar--H). Rf (I)=0.62, Rf (VI)=0.38.

Workup

  1. stirringAfter stirring for 4 hrs at 0° C.
  2. stirringthe reaction mixture was stirred at room temperature overnight
  3. filtrationthe precipitated crystals were filtered
  4. customthe filtrate was evaporated in vacuo
  5. extractionThe residue was extracted with ethyl acetate
  6. washthe extract was washed with 5% citric acid, 5% NaHCO3 and water successively
  7. customdried over anhyd
  8. customThe solvent was removed in vacuo
  9. customthe resulting solid was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-b72e596b62b244219d053187931f1834
Source dataset
uspto-grants-1986_12
Patent number
US04629784

Reaction notes

Loading…